Milk begins on Harvey Milk's 40th birthday (in 1970), when he was living in New York City and had not yet settled in San Francisco. It chronicles his foray into city politics, and the various battles he waged in the Castro neighborhood as well as throughout the city, and political campaigns to limit the rights of gay people in 1977 and 1978 run by Anita Bryant and John Briggs. His romantic and political relationships are also addressed, as is his tenuous affiliation with troubled Supervisor Dan White; the film ends with White's double homicide of Milk and Mayor George Moscone. The film's release was tied to the 2008 California voter referendum on gay marriage, Proposition 8, when it made its premiere at the Castro Theatre two weeks before election day.

Dissatisfied with his life and in need of a change, Milk and Smith decide to move to San Francisco in the hope of finding larger acceptance of their relationship. They open Castro Camera in the heart of Eureka Valley, a working-class neighborhood in the process of evolving into a predominantly gay neighborhood known as The Castro. Frustrated by the opposition they encounter in the once Irish-Catholic neighborhood, Milk utilizes his background as a businessman to become a gay activist, eventually becoming a mentor for Cleve Jones (Emile Hirsch). Early on, Smith serves as Milk's campaign manager, but he grows frustrated with Milk's devotion to politics, and he leaves him. Milk later meets Jack Lira (Diego Luna), a sweet-natured but unbalanced young man. As with Smith, Lira cannot tolerate Milk's devotion to political activism, and eventually hangs himself. Milk clashes with the local gay "establishment" which he feels to be too cautious and risk-averse.

After two unsuccessful political campaigns in 1973 and 1975 to become a city supervisor and a third in 1976 for the California State Assembly, Milk finally wins a seat on the San Francisco Board of Supervisors in 1977 for District 5. His victory makes him the first openly gay man to be voted into major public office in California and the third openly homosexual politician in the entire US. Milk subsequently meets fellow Supervisor Dan White (Josh Brolin), a Vietnam veteran and former police officer and firefighter. White, who is politically and socially conservative, has a difficult relationship with Milk, and develops a growing resentment for Milk when he opposes projects that White proposes.

Milk and White forge a complex working relationship. Milk is invited to, and attends, the christening of White's first child, and White asks for Milk's assistance in preventing a psychiatric hospital from opening in White's district, possibly in exchange for White's support of Milk's citywide gay rights ordinance. When Milk fails to support White because of the negative effect it will have on troubled youth, White feels betrayed, and ultimately becomes the sole vote against the gay rights ordinance. Milk also launches an effort to defeat Proposition 6, an initiative on the California state ballot in November 1978. Sponsored by John Briggs (Denis O'Hare), a conservative state legislator from Orange County, Proposition 6 seeks to ban gays and lesbians (in addition to anyone who supports them) from working in California's public schools. It is also part of a nationwide conservative movement that starts with the successful campaign headed by Anita Bryant and her organization Save Our Children in Dade County, Florida to repeal a local gay rights ordinance.

On November 7, 1978, after working tirelessly against Proposition 6, Milk and his supporters rejoice in the wake of its defeat. A desperate White favors a supervisor pay raise, but does not get much support, and shortly after supporting the proposition, resigns from the Board. He later changes his mind and asks to be reinstated. Mayor Moscone denies his request, after being lobbied by Milk.

On the morning of November 27, 1978, White enters City Hall through a basement window to conceal a gun from metal detectors. He requests another meeting with Moscone, who rebuffs his request for appointment to his former seat. Enraged, White shoots Moscone in his office and then goes to meet Milk, where he guns him down, with the fatal bullet delivered execution-style. The film suggests that Milk believed that White might be a closeted gay man.[3]

The last scene is a candlelight vigil held by thousands for Milk and Moscone throughout the streets of the city. Pictures of the actual people depicted in the film, and brief summaries of their lives follow.

A number of Milk's associates, including speechwriter Frank M. Robinson, Teamster Allan Baird and school teacher-turned-politician Tom Ammiano portrayed themselves. Additionally, Carol Ruth Silver, who served with Milk on the Board of Supervisors, plays a small role as Thelma. Cleve Jones also has a small role as Don Amador. Anne Kronenberg makes a cameo appearance as a stenographer, and Daniel Nicoletta appears in a cameo as Carl Carlson.

The production design and costume design crew for the film researched the history of the city's gay community in the archives of the GLBT Historical Society in San Francisco, where they spent several weeks reviewing photographs, film and video, newspapers, historic textiles and ephemera, as well as the personal belongings of Harvey Milk, which were donated to the institution by the estate of Scott Smith.[14][15] The crew also talked to people who knew Milk to shape their approach to the era.

The filmmakers also revisited the location of Milk's camera shop on Castro Street and dressed the street to match the film's 1970s setting. The camera shop, which had become a gift shop, was bought out by filmmakers for a couple of months to use in production. Production on Castro Street also revitalized the Castro Theatre, whose facade was repainted and whose neon marquee was redone. Filming also took place at the San Francisco City Hall, while White's office, where Milk was assassinated, was recreated elsewhere due to the city hall's offices having become more modern. Filmmakers also intended to show a view of the San Francisco Opera House from the redesign of White's office.[16] Filming finished March 2008.[17]

In the month leading up to Milk's release, Focus Features kept the film out of all film festivals and restricted media screenings, seeking to briefly avoid word-of-mouth and the partisanship it could generate. Milk premiered in San Francisco on October 28, 2008, initiating a marketing dilemma that Focus Features struggled to face due to the film's subject matter. The studio hoped to stay above the politics of the ongoing general elections, especially California's anti-gay-marriage Proposition 8, which parallels the anti-gay rights Proposition 6 that is explored in the film.[18]

Regardless, many reviewers and pundits have noted that the highly acclaimed film has taken on a new significance after the successful passage of Proposition 8 as a galvanizing point of honoring a major gay political and historical figure who would have strongly opposed the measure.[19][20] Gay activists called on Focus Features to pull the film from the Cinemark Theatres chain as part of a series of boycotts because Cinemark's chief executive, Alan Stock, donated $9,999 to the Yes on 8 campaign.[21][22]

In the United States, Milk was given a limited release on November 26, 2008, and expanded to additional theaters each of the following weekends to a maximum of 882 screens. The film made the top 10 box office list on its opening weekend with earnings of $1.4 million in 36 theaters.[23] At the box office, the film more than doubled its production cost of $20 million. However, its long-term box office receipts were relatively poor.[24]

Milk received universal critical acclaim, with Penn's performance receiving rave reviews.[27]Rotten Tomatoes reported that 94% of critics gave the film a positive review, based on a sample of 211, with an average score of 8.0/10.[28] At Metacritic, which assigns a rating out of 100 to reviews from mainstream critics, the film has received an average score of 84, based on 39 reviews.[27]

Todd McCarthy of Variety called the film "adroitly and tenderly observed," "smartly handled," and "most notable for the surprising and entirely winning performance by Sean Penn." He added, "while Milk is unquestionably marked by many mandatory scenes . . . the quality of the writing, acting and directing generally invests them with the feel of real life and credible personal interchange, rather than of scripted stops along the way from aspiration to triumph to tragedy. And on a project whose greatest danger lay in its potential to come across as agenda-driven agitprop, the filmmakers have crucially infused the story with qualities in very short supply today — gentleness and a humane embrace of all its characters."[29]

Kirk Honeycutt of The Hollywood Reporter said the film "transcends any single genre as a very human document that touches first and foremost on the need to give people hope" and added it "is superbly crafted, covering huge amounts of time, people and the zeitgeist without a moment of lapsed energy or inattention to detail . . . Black's screenplay is based solely on his own original research and interviews, and it shows: The film is richly flavored with anecdotal incidents and details. Milk surfaces in a season filled with movies based on real lives, but this is the first one that inspires a sense of intimacy with its subjects."[30]

A. O. Scott of The New York Times called Milk, "A Marvel", and wrote the film "is a fascinating, multi-layered history lesson. In its scale and visual variety it feels almost like a calmed-down Oliver Stone movie, stripped of hyperbole and Oedipal melodrama. But it is also a film that like Mr. Van Sant's other recent work — and also, curiously, like David Fincher's Zodiac, another San Francisco-based tale of the 1970s — respects the limits of psychological and sociological explanation."[31]

Christianity Today, a major Evangelical Christian periodical, gave the film a positive response.[19] It stated that "Milk achieves what it sets out to do, telling an inspiring tale of one man's quest to legitimize his identity, to give hope to his community. I'm not sure how well it'll play outside of big cities, or if it will sway any opinions on hot-button political issues, but it gives a valiant, empathetic go of it." It also stated that the portrayal of Dan White was very fair and humanized and portrayed as more of a tragically flawed character, rather than a "typical 'crazy Christian villain' stereotype".[19]

In contrast, John Podhoretz of the conservative magazine Weekly Standard blasted the portrayal of Harvey Milk, saying that it treated the "smart, aggressive, purposefully offensive, press-savvy" activist like a "teddy bear". Podhoretz also argued that the film glosses over Milk's polyamorousrelationships; he opined that this contrasts Milk from present day gay rights activists fighting over monogamoussame-sex marriage. Podhoretz mentioned as well that the film concentrates on Milk's opposition to the Briggs Initiative while ignoring that both Governor Ronald Reagan and President Jimmy Carter had made more public statements against it.[32]

Screenwriter and journalist Richard David Boyle, who described himself as a former political ally of Milk's, stated that the film made a creditable effort of recreating the era. He also wrote that Penn captured Milk's "smile and humanity", and his sense of humor about his homosexuality. Boyle reserved criticism for what he felt was the film's inability to tell the whole story of Milk's election and demise.[33]

Luke Davies of The Monthly applauded the film for recreating "the atmosphere, the sense of hope and battle; even the sound design, bustling with street noise, adds much vibrancy to the tale," but voiced criticisms in regard to the message of the film, stating "while the film is a political narrative in a grand historical sense, the murder of Milk is neither a political assassination nor an act of homophobic rage. Rather, it is an act of revenge for perceived wrongs and public humiliation," Davies continues to postulate that "It seems as likely that Milk would have been murdered were he heterosexual. So the film can't be the heroic tale of a political martyr it needs to be in order to hold us and take our breath away. It's a simpler story, about a man who fought an extraordinary political fight and who was killed, arbitrarily and unnecessarily." Although Davies found Penn's portrayal of Milk moving, he adds that "on a minor but troubling note, there are times when Penn's version of 'gay' acting veers dangerously close to a twee version of his childlike (read: 'mentally retarded') acting in I Am Sam." All his criticisms aside, Davies concludes that "the heart of the film — and while it is not perfect, it is uplifting — lies in Penn's portrayal of Milk's generosity of spirit.[34]

The film appeared on many critics' top ten lists of the best films of 2008.[36] Movie City News shows that the film appeared in 131 different top ten lists, out of 286 different critics lists surveyed, the 4th most mentions on a top ten list of the films released in 2008.[37]

Listed - Roger Ebert, Chicago Sun-Times[36] (Ebert gave a top 20 list in alphabetical order without ranking and announced on his website that he considered it the most deserving 2008 'Best Picture' nominee at the Oscars.)

In late March 2009, Samoa's Censorship Board banned the film from distribution, without giving a reason.[38] Samoan human rights activist Ken Moala disputed the ban, commenting that "It's really harmless, I don't know how it would affect Samoan lifestyle. It is totally different and not applicable to here, it is pretty tame really."[38] The Pacific Freedom Forum issued a press release stating that "Samoa is the only nation worldwide where censors have specifically banned the multi-academy award winning film," limiting Samoans to smuggled or pirated versions.[39]American Samoan Monica Miller, the Forum's co-chair, stated, "Observers are left to wonder at the censorship standards being applied in a country where fa'afafine have a well established and respected role."[39] Fa'afafine are biologically men raised to assume female gender roles, making them a third gender well accepted in Samoan society. The Fa'afafine Association also criticised the ban, describing it as a "reject[ion of] the idea of homosexuality".[40]

On April 30, Principal Censor Leiataua Niuapu released the reason for the ban, saying the film had been deemed "inappropriate and contradictory to Christian beliefs and Samoan culture": "In the movie itself it is trying to promote the human rights of gays. Some of the scenes are very inappropriate in regard to some of the sex in the film itself, it's very contrary to the way of life here in Samoa."[41] Samoan society is, in the words of the BBC, "deeply conservative and devoutly Christian".[42]

December 9, 2008, the film received eight Critic's Choice Award nominations, including Best Picture and Best Director.

December 11, 2008, Sean Penn received one Golden Globe nomination for Best Actor, the film's only nomination.

December 18, 2008, the Screen Actors Guild nominated Milk in three categories: Best Actor, Best Supporting Actor and Best Cast in a Motion Picture for the 15th Screen Actors Guild Awards; Sean Penn was chosen as Best Actor.

January 5, 2009, the film's producers received a nomination for Producer of the Year for the 20th Producers Guild of America Awards.